A series of novel 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine linked various sulfonamide derivatives 8a-8j poly functionalized were designed and synthesized in moderate to good yield. A starting with iodination of 5-Bromo-1H-pyrazolo[3,4-b]pyridine 5 with iodine produced intermediate 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine 6 with the reaction of various sulfonamide derivatives 7a-7j via copper catalyzed coupling reaction produced targeted compounds8a-8j. The isolated compounds were accepted by spectral and elemental analysis. The compounds 8a,8c,8d, and 8i were excellent active against Gram-positive and gram-negative bacterial strain compare to streptomycin standard drug. All synthesized compounds showed moderate to good antioxidant properties with used DPPH and Superoxide radical scavenging assay, Compounds 8c, 8g, and 8i exerted significant antioxidant scavenging activity for the DPPH radical.